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We present the synthesis and characterization of DTPA-bis(histidylamide) (1a), DTPA-bis(aspartamide) (1b), and their gadolinium complexes of the type (2a:L = 1a; 2b:L = 1b). Thermodynamic stabilities and relaxivities of 2a-b compare well with Omniscan, a well-known commercial, extracellular (ECF) MRI CA which adopts the DTPA-bis(amide) framework for the chelate: = 5.5 and 5.1 for 2a and 2b, respectively. Addition of the Cu(II) ion to a solution containing 2b triggers relaxivity enhancement to raise as high as 15.3 , which corresponds to a 300% enhancement. Such an increase levels off at the concentration beyond two equiv. of Cu(II), suggesting the formation of a trimetallic () complex in situ. Such a relaxivity increase is almost negligible with Zn(II) and other endogenous ions such as Na(I), K(I), Mg(II), and Ca(II). In vivo MR images and the signal-to-noise ratio (SNR) obtained with an aqueous mixture of 2b and Cu(II) ion in an 1:2 ratio demonstrate the potentiality of 2 as a copper responsive MRI CA.

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Gadolinium Complexes of Bifunctional Diethylenetriaminepentaacetic Acid (DTPA)-bis(amides) as Copper Responsive Smart Magnetic Resonance Imaging Contrast Agents (MRI CAs)